Stats: 64 miles, 6,297-ft of climb

Download the route here!

Pre-ride notes

What to wear

Layers are going to be essential on this ride for the best temperature regulation. The temperature can drop by 10 or so degrees at the peaks of the climbs around Skyline boulevard and persist until you reach sea level. If you don’t prepare correctly, the shady descents can feel bitterly cold. The coast can also be a bit cooler and windier area than the inner peninsula. To accomodate for the Bay’s cool spring and summer mornings, I prefer to wear a base layer, short sleeve jersey with arm-warmers, and a light wind breaking vest. This combination helps me keep warm when I need it, with the option to shed a few layers if I choose to on the warmer sections. A pair of light gloves could also be added to keep your fingers nice and warm.

How to fuel your ride

Packing enough nutrition is also crucial if you want to have an enjoyable experience, much like any other ride! Aim to consume between 30 and 90 grams of carbohydrates per hour — depending on how hard you want to go. Keeping yourself fueled early and often is the key to having enough energy in the legs for that final climb back up to skyline on Tunitas Creek road. You can choose from a variety of carbohydrate sources, but my favorite are sport drink mixes with high carb content, gels, cliff or Rx bars, and pop-tarts!

The Route

Cañada and Woodside

My favorite way to start this ride is on Cañada Road. It has both ample parking and scenic views of the Crystal Springs Reservoir, over gently rolling hills. On Sundays, the beginning 2.7 miles are car-free and because of this, you can easily see a few hundred cyclists riding along it on any given weekend. Lots of group rides and solo riders overtake the road which makes it prime for showing off that new fresh kit – or for me, just a freshly washed kit. Cañada Road is just over 7 miles long with only two all-way stops closer to Woodside. Use caution when rolling through this area because cops like to sit and wait for you to roll it!

Once in Woodside, the most direct route over to our first climb is Mountain Home road. This undulating and shady road is lined with huge Eucalyptus that stand guarding the parallel foot trail. The trail is flowy single-track that gets mostly pedestrian and equestrian attention, but is confidently bike-able with some grippier tires.

From Mountain Home, you’ll reach a 3 way intersection and turn left – narrowly avoiding the inconspicuous curbed wedge that is raised from the intersection of Mountain Home and Portola road, then turn right continuing onto Portola road. You’ll stay on Portola just a short while and turn onto Old La Honda to begin your 1,250-ft ascent.

Old La Honda (OLH) climb

The Old La Honda climb is the beast that stands between you and skyline at the top of the mountain. It’s short and punchy at an average gradient of 8% – and well traveled most weekend mornings. A mark of fitness is earned if you can complete the climb in 20 minutes or less – a nominal time determined by one of the dominating cycling clubs in the area, Alto Velo. The climb starts off with a steep and sweeping left curve where it rounds against the mountainside weaving through residential mountain chateaus. Don’t be too temped to unleash your power until the second half of the climb though. The punchy bits of the climb peak at around 14% for the first half but increase to 20% in the second half, so you’ll want to save your legs and lungs until then. 

As you climb higher and higher, it is crucial to remember your place as a cyclist and stay at the right side of the road! While, technically a flagged descent on strava, you will catch some folks ripping down the road as you ascend. So as you are flatlining try to keep your attention focused on your spatial awareness. There is one section of road on the climb that narrows between large redwoods, turning into a single lane. 

As your muscles begin tearing, you might look up to see one road mocking your effort called “Upenuf road”. I would agree that once you reach this point, you might have indeed gone up enough.

OLH peaks out at 1,700-ft at skyline road, where you’ll most likely encounter a number of riders out on their day recovering or chatting while having a snack. This intersection is a common re-grouping spot for the surrounding weekend group rides. After regaining the consciousness you lost from your hard effort, plunge yourself down the dark hole across the road to continue your journey. A cool and shady descent takes you back to the mother-road, La Honda. 

(Taking the road to your right which heads north on Skyline, will leads you to a popular hotspot including Alice’s Restaurant. No, its not the famous Alice’s Restaurant that Arlo Gutrhie sang about but it is locally famous as a supercar and motorcycle meetup spot. Across the way is a market good for stocking up on some ride nutrition.)

La Honda and Pescadero 

La Honda is a twisty descent that has a handful of sharp corners. Excellent for practicing your descending skills, but be weary of the potholes, cracks, and gravel that may lie in the shadows on this section of road. To crash on this side of the mountain, would leave you wounded and in isolation on this remote side of the mountain. 

You will probably experience a vast array of microclimates as you descend into the other side of the mountain range. I’ve mostly experienced chilling cold pockets on the way down that make me wish I had packed just one more layer. 

The road down through the valley is a fast one for other motorists, especially on weekends. It’s nothing to be too afraid of when route planning, but some of the riding/driving clubs will take their fast sports cars out on this road, and the possibility of getting buzzed is always there. So take caution on this road and the next pescadero, which is our next climb.

Climbing out of the valley is not nearly as hard as getting into it, fortunately. Pescadero is a short, 2.5-km climb of about 6.8% according to Strava – and definitely not as challenging as the Old La Honda climb. Its a perfect climb to get your legs spinning after that long descent down La Honda.

From the top of Pescadero, you’ll begin your final descent before reaching an espresso and some rest. Strava’s segment for this descent is a tad bit misleading, as it claims the 8-km section of downgrade is only about -3.7%, though booking at the elevation profile, you can see the steepest sections shoot you downward about 800-feet in 3km. Though, the following sections of the road are nice and flowy – smooth enough to eat a quick snack and maintain some speed, but still not terrifyingly fast. 

Pit stop in Pescadero

As the road flattens, you feel like you just woke up from a dream. The shady and cool redwood forests that you became so familiar with have all receded behind you, yielding to windy coastal farmland. Though there is no need to worry, Pescadero is just a mile or so away! As you roll into town, hoards of cyclists sit sipping their cappuccinos on the small patio furniture of the first coffee shop you pass. Some may give you a keen eyeball, but they’re probably just checking out that sweet kit you’re riding in or the steed that just took you over and down the mountain. 

The one café i town, called the Downtown Local, is a small shop that not only houses caffeinated beverages and baked goods, but also some trippy antiques from the 70’s and Beatles vibes. Reviews for the shop are somewhat mixed on Yelp, mainly with regards to the questionable service, depending on who is working – so caffeinate at your own risk. 

Next stop in town is Arcangeli’s grocery for some of their famous artichoke bread. You will definitely regret skipping out on these delicious carbs. Take your loaf around back to find a pleasant little park area with some nice picnic benches and you’ll soon forget you were in the middle of a 64 mile ride.

As you make your way out, make sure to fill your bottles at the bottle spigot just at the side of the building. The next portion of the road, Stages, is a series of 3 shorter climbs that take you to Highway 1.

Stage road

The road out of town takes you past a cemetery which marks the start of the climbing. Three miles to the top of the first 430-ft climb which rewards you with a beautiful view of the pacific ocean. 

The descents are fast, sweeping, and fun as they propel you around the exposed mountainside, but since they lack any good tree coverage, the west winds from the pacific smack you right in the soft spot. The last peak spits you at a right turn onto Highway 1, which parallels the coast and descends to Tunitas Creek road. This descent is wide open and fast, with cars passing even faster to the left of you. The ocean slaps the cliffside, coaxing you to pay attention to its magnificence, but the high winds and passing cars jolt you back from your cinematic dissociations. The bike lanes here are fairly wide for most of the descent until just before the turn onto Tunitas Creek. As you cross over a bridge the bike lane recedes, so you should be careful when overtaking the lane. A mindful eye and early overtaking of the road will allow you to safely cross this bridge. After making the turn onto Tunitas Creek Road, you’ll soon pass a self-serve coffee hut which sits on the side of the road. It’s bright red and hard to miss if you need that last-minute caffeine boost before entering the pain cave one last time.

Tunitas Creek Climb

A long climb of roughly 9 miles starts once you make that turn onto Tunitas begins with a deceptive false flat. The first two miles ascend barely 40 feet in elevation. The next mile adds about 120ft of vertical climb, and the following mile adds about 300ft. Winding its way from the open coastal plain back into the dense forests, the changing vegetation provides cool shade for your ascent. The climb then starts to feel really steep, hovering at a whopping 9% average grade for almost 2 miles. All you need to do is hold out until mile 7 when the gradient significantly drops back to a seemingly false flat until you reach the top at Skyline. The last two miles are so flowy, you’ll actually carry momentum through the corners if you take them right. Before you know it, you’re back up the mountain  –waiting at the intersection of Tunitas, Kings Mountain, and Skyline Blvd. This is a great spot to rest and wait for fellow riders that you dropped earlier on the ride.

The descent down King’s Mountain

The descent down King’s Mountain isn’t particularly technical, but it is fast. Flowy corners open up to fast and relatively straight sections of road where your speed can pick up quite quickly. The 4 sharp corners along the route call for some heavier breaking depending on your risk tolerance, but for a seasoned descender, they shouldn’t be too intimidating. Once you pass Huddart Park, the hardest part is over and you get to enjoy the rest of your cruise.

Crossing back into Woodside marks the final stretch of your ride. From the junction, it’s 7 miles back to the end of Cañada road. Time to crack open those victory beers and slow roll on the remaining miles to give your legs some breathing room. Congratulations, you just finished a Bay Area classic.